Jump to main content
Jump to site search


Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding

Author affiliations

Abstract

By systematic measurements we have evaluated a series of tetraphenyl metalloporphyrins and halogenated tetraphenyl metalloporphyrin derivatives for binding to ligands with oxygen containing functional groups, using methanol, acetic acid and acetone as examples. Experimental binding constants identified three metalloporphyrins with good binding to all three ligands: MgTPFPP, MgTPPBr8 and ZnTPPBr8 as well as a range of porphyrins binding to select ligands. Based on these results the optimal porphyrins can be selected for the desired binding interactions. We also show how to use DFT calculations to evaluate the potential binding between a metalloporphyrin and a ligand, which is deduced from free energies of binding ΔG, charge transfer ΔQ, and change of metal spin state. Computations on unsubstituted porphyrins in lieu of tetraphenyl porphyrin systems yield reliable predictions of binding interactions with good correlation to the corresponding experimental data. The calculations have also yielded interesting insights into the effect of halogenation in the β-position on the binding to ligands with oxygen containing functional groups.

Graphical abstract: Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding

Back to tab navigation

Supplementary files

Publication details

The article was received on 13 Jun 2018, accepted on 26 Jul 2018 and first published on 01 Aug 2018


Article type: Paper
DOI: 10.1039/C8DT02432D
Citation: Dalton Trans., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding

    S. Olsson, C. Dahlstrand and A. Gogoll, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C8DT02432D

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements